diff --git a/travis/macos-install.sh b/travis/macos-install.sh
index 987dbb5..f1a88d0 100755
--- a/travis/macos-install.sh
+++ b/travis/macos-install.sh
@@ -5,9 +5,11 @@ set -ex
 export HOMEBREW_NO_INSTALL_CLEANUP=1
 
 # Python 3.7.4 with 10.12 bottle
-brew install openssl@1.1
 brew upgrade https://raw.githubusercontent.com/Homebrew/homebrew-core/e9004bd764c9436750a50e0b428548f68fe6a38a/Formula/python.rb
 
+# Reinstall openssl to fix Python pip install issues
+brew reinstall openssl@1.1
+
 which python3
 python3 --version
 which pip3
@@ -21,6 +23,7 @@ brew upgrade https://raw.githubusercontent.com/Homebrew/homebrew-core/dcc34dd3cb
 
 python3 -c "from PySide2 import __version__; print(__version__)"
 python3 -c "from PySide2.QtCore import __version__; print(__version__)" 
+python3 -c "import ssl; print(ssl)"
 pip3 install py2app
 python3 -c "from py2app.recipes import pyside2"
 pip3 install twisted[tls] appnope requests certifi